NPASS Compound

Natural Product: NPC591983

Natural Product ID	NPC591983
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2~{S})-2-[(~{Z})-hexadec-9-enoyl]oxy-3-[(2~{R},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-propyl] (~{Z})-hexadec-9-enoate
IUPAC Name	[(2~{S})-2-[(~{Z})-hexadec-9-enoyl]oxy-3-[(2~{R},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-propyl] (~{Z})-hexadec-9-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 125125 0 0 0 0 0 0 0 0999 V2000 -12.9089 6.4430 -2.0012 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5999 5.1405 -2.1454 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.4544 4.1680 -1.0464 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0852 3.6734 -0.7815 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0527 4.6533 -0.3736 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7462 3.8929 -0.0955 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2185 3.1989 -1.2789 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0307 3.4482 -1.7922 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0980 4.4306 -1.2572 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7666 3.7768 -0.8498 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0881 2.7284 0.1719 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8601 1.9782 0.6703 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3019 0.9351 1.6544 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1341 0.1639 2.1837 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 -0.5145 1.0873 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2763 -1.2958 1.7541 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4647 -2.5425 1.9812 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0767 -0.7502 2.1349 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0370 -1.4392 2.7485 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5276 -2.5047 1.9032 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5535 -3.3799 2.6675 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7834 -4.4874 1.8856 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6751 -5.4117 2.4001 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6602 -5.6289 1.4489 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1908 -6.8871 1.4117 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2867 -6.8785 0.3327 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8761 -8.1397 0.2385 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2409 -7.9823 1.0085 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2786 -8.2408 -0.3579 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8435 -7.5581 1.3995 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2767 -6.7252 0.4305 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9915 -6.7444 2.6648 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7548 -7.4771 3.5641 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1022 -2.1547 0.7017 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8824 -2.6276 -0.5540 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0282 -3.5366 -0.6827 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5852 -2.1261 -1.7342 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6634 -1.0989 -1.3302 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6997 -1.7585 -0.5226 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8666 -0.9225 -0.1230 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5801 0.2948 0.6397 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9379 1.4586 -0.0034 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9333 2.0537 -1.0479 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0920 2.5435 -0.3034 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3630 2.2206 -0.4441 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8444 1.2719 -1.4250 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7921 1.6736 -2.4723 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1232 2.1980 -2.1933 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2540 3.4955 -1.4610 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7466 3.8782 -1.3308 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4794 2.8167 -0.5585 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.6390 7.2434 -2.3440 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0375 6.6017 -2.6811 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6155 6.7093 -0.9893 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.7030 5.2582 -2.3407 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2275 4.6783 -3.1178 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.1865 3.3045 -1.1775 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.8109 4.6638 -0.0857 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1517 2.8383 -0.0141 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6699 3.1186 -1.6815 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7999 5.3208 -1.2374 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3540 5.2832 0.4664 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0925 4.5843 0.4099 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0058 3.0930 0.6691 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8377 2.4203 -1.7633 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7543 2.8583 -2.6844 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4379 4.9889 -0.4061 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7817 5.1896 -2.0443 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1976 4.6143 -0.3503 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2396 3.3960 -1.7274 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7288 1.9497 -0.3219 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6398 3.1879 1.0105 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3624 1.4528 -0.1921 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1277 2.6764 1.0837 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8766 1.4065 2.4847 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0015 0.1966 1.2001 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4606 -0.5365 2.9795 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4615 0.8976 2.6838 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9234 0.2137 0.3680 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9786 -1.2166 0.5066 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5108 -1.9631 3.6364 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7145 -0.7775 3.2275 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2846 -3.2627 1.6853 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2295 -3.5773 3.6855 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4813 -2.7745 2.7015 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0755 -5.0589 3.3773 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7138 -7.1972 2.3577 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7834 -6.5766 -0.6083 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0358 -6.0998 0.5587 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3303 -8.8503 0.6205 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4469 -8.9223 1.5927 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5036 -8.8236 -0.5691 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1790 -8.4124 1.6468 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2998 -6.9456 0.4022 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9695 -6.6016 3.0719 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2286 -8.1776 4.0262 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0727 -2.9144 -2.3356 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9163 -1.5684 -2.4414 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9774 -0.5413 -2.2001 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0375 -0.4205 -0.6598 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0806 -2.7114 -1.0425 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2431 -2.1933 0.4065 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4726 -0.7201 -1.0576 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5478 -1.6268 0.4727 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5774 0.6398 1.1037 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9858 0.0695 1.5860 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0242 1.3645 -0.5479 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7853 2.2726 0.7797 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3608 2.9269 -1.4632 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1010 1.2639 -1.7699 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8665 3.2840 0.4803 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0288 2.7203 0.2834 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3568 0.4305 -0.8389 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0112 0.7117 -1.9368 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2837 2.3615 -3.2460 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9228 0.7343 -3.1341 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6432 2.3279 -3.2044 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7242 1.3875 -1.6474 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9256 3.3892 -0.4235 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7674 4.2949 -2.0235 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1479 3.9436 -2.3523 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7899 4.8344 -0.7698 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0629 2.1735 -1.2224 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7167 2.1933 -0.0409 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1458 3.2772 0.2120 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 20 34 1 0 34 35 1 0 35 36 2 0 35 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 32 23 1 0 1 52 1 0 1 53 1 0 1 54 1 0 2 55 1 0 2 56 1 0 3 57 1 0 3 58 1 0 4 59 1 0 4 60 1 0 5 61 1 0 5 62 1 0 6 63 1 0 6 64 1 0 7 65 1 0 8 66 1 0 9 67 1 0 9 68 1 0 10 69 1 0 10 70 1 0 11 71 1 0 11 72 1 0 12 73 1 0 12 74 1 0 13 75 1 0 13 76 1 0 14 77 1 0 14 78 1 0 15 79 1 0 15 80 1 0 19 81 1 0 19 82 1 0 20 83 1 6 21 84 1 0 21 85 1 0 23 86 1 1 25 87 1 1 26 88 1 0 26 89 1 0 27 90 1 0 28 91 1 1 29 92 1 0 30 93 1 1 31 94 1 0 32 95 1 1 33 96 1 0 37 97 1 0 37 98 1 0 38 99 1 0 38100 1 0 39101 1 0 39102 1 0 40103 1 0 40104 1 0 41105 1 0 41106 1 0 42107 1 0 42108 1 0 43109 1 0 43110 1 0 44111 1 0 45112 1 0 46113 1 0 46114 1 0 47115 1 0 47116 1 0 48117 1 0 48118 1 0 49119 1 0 49120 1 0 50121 1 0 50122 1 0 51123 1 0 51124 1 0 51125 1 0 M END

Standard InCHIKey	JEVHYEXEBHQRHN-NRKRSWHCSA-N
Standard InCHI	InChI=1S/C41H74O10/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(43)48-32-34(33-49-41-40(47)39(46)38(45)35(31-42)51-41)50-37(44)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,34-35,38-42,45-47H,3-12,17-33H2,1-2H3/b15-13-,16-14-/t34-,35-,38+,39+,40-,41-/m1/s1
SMILES	CCCCCC/C=CCCCCCCCC(=O)OC[C@H](CO[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)OC(=O)CCCCCCC/C=CCCCCCC

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO61385	Nitzschia sp.	Species	Bacillariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC591983 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	18120
0.1-0.2	24922
0.2-0.3	5864
0.3-0.4	782
0.4-0.5	92
0.5-0.6	53
0.6-0.7	8
0.7-0.8	0
0.8-0.85	5
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC488689
0.9455	High Similarity	NPC21693
0.9123	High Similarity	NPC156089
0.8846	High Similarity	NPC488690
0.8772	High Similarity	NPC236649
0.8475	Intermediate Similarity	NPC110813
0.8387	Intermediate Similarity	NPC470313
0.8387	Intermediate Similarity	NPC473500
0.8387	Intermediate Similarity	NPC611497
0.8065	Intermediate Similarity	NPC38295
0.7869	Intermediate Similarity	NPC133377
0.746	Intermediate Similarity	NPC488694
0.7246	Intermediate Similarity	NPC22558
0.7121	Intermediate Similarity	NPC488692
0.6833	Remote Similarity	NPC83839
0.6667	Remote Similarity	NPC476612
0.6667	Remote Similarity	NPC476613
0.6508	Remote Similarity	NPC488693
0.6406	Remote Similarity	NPC331437
0.6216	Remote Similarity	NPC476611
0.6207	Remote Similarity	NPC206601
0.6	Remote Similarity	NPC54925
0.5902	Remote Similarity	NPC285003
0.5893	Remote Similarity	NPC48218
0.5893	Remote Similarity	NPC141481
0.5893	Remote Similarity	NPC464342
0.5873	Remote Similarity	NPC469469
0.5846	Remote Similarity	NPC489083
0.5738	Remote Similarity	NPC12040
0.5593	Remote Similarity	NPC473559
0.5593	Remote Similarity	NPC324981
0.5556	Remote Similarity	NPC104537
0.5455	Remote Similarity	NPC163812
0.5352	Remote Similarity	NPC282705
0.5352	Remote Similarity	NPC263545
0.5352	Remote Similarity	NPC242503
0.5352	Remote Similarity	NPC182632
0.5352	Remote Similarity	NPC473950
0.5352	Remote Similarity	NPC111567
0.5352	Remote Similarity	NPC186840
0.5352	Remote Similarity	NPC144916
0.5352	Remote Similarity	NPC486421
0.5352	Remote Similarity	NPC309898
0.5352	Remote Similarity	NPC273493
0.5352	Remote Similarity	NPC475125
0.5352	Remote Similarity	NPC486419
0.5352	Remote Similarity	NPC15851
0.5352	Remote Similarity	NPC115448
0.5352	Remote Similarity	NPC20819
0.5352	Remote Similarity	NPC486418
0.5352	Remote Similarity	NPC473604
0.5352	Remote Similarity	NPC486420
0.5352	Remote Similarity	NPC479188
0.5352	Remote Similarity	NPC81468
0.5303	Remote Similarity	NPC250619
0.5286	Remote Similarity	NPC43074
0.5286	Remote Similarity	NPC139782
0.5286	Remote Similarity	NPC74672
0.5286	Remote Similarity	NPC61894
0.5286	Remote Similarity	NPC209047
0.5286	Remote Similarity	NPC297079
0.5263	Remote Similarity	NPC330426
0.5263	Remote Similarity	NPC127091
0.5263	Remote Similarity	NPC22101
0.5263	Remote Similarity	NPC606861
0.5263	Remote Similarity	NPC607126
0.5238	Remote Similarity	NPC241265
0.5192	Remote Similarity	NPC55678
0.5135	Remote Similarity	NPC158445
0.5135	Remote Similarity	NPC157353
0.5135	Remote Similarity	NPC282088
0.5132	Remote Similarity	NPC488691
0.5091	Remote Similarity	NPC148192
0.5079	Remote Similarity	NPC76881
0.5068	Remote Similarity	NPC602861

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC591983 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6491
0.1-0.2	2457
0.2-0.3	168
0.3-0.4	28
0.4-0.5	4
0.5-0.6	2
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5286	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5192	Remote Similarity	NPD6125	Phase 4

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data